


Finding my Place

by sallyvera91



Category: Teen Wolf (TV)
Genre: Exhibitionism, F/M, Falling In Love, Female Stiles Stilinski, Hairy Derek, Hairy Derek Hale, Jock Derek Hale, Multiple Orgasms, Other, Possessive Behavior, Protective Derek, Top Derek Hale, Trans Character, Trans Female Character, True Love
Language: English
Status: In-Progress
Published: 2016-02-18
Updated: 2016-02-24
Packaged: 2018-05-21 10:29:13
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 3,571
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6048181
Author URL: https://archiveofourown.org/users/sallyvera91/pseuds/sallyvera91
Summary: <blockquote class="userstuff">
              <p>Stiles, I mean Stella, is in the middle of her transition when she meets a real man. One problem, she is taken.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> First fic!

My name is Stella Stilinski, and this is the story of how I found my true calling. My life today is completely different from what it was a month ago, before I met Derek. Let me start there. 

 

One December morning. I had just finished my morning jog and was showering. I love to take long hot showers because the hot water relaxes my body after I go for runs. I love feeling the hot water run down my breasts. My sensitive nipples especially love the sensation. The water runs in between my legs onto my uncut 7 inch cock. It’s longer than average, but pretty skinny, like the rest of me now. 

 

It was 7am and I walked past my boyfriend of four years. His name was Matt. And despite being 32 he was more boy than man. I met him while attending UCLA, I was an undergrad and he was getting his masters. Back when we started dating he had so much potential.  He wasn't fat, and had majored in engineering. 

 

Today. He's 5’8 and nearly 200 pounds. It's hard for me to look at him sometimes. I know he won't wake up for another two hours. He hasn't managed to find a job with his degree and he's stuck in a middle management position. 

 

When we started dating he was really supportive of my transition. I've always been cute but chubby. Pale soft skin, with moles sprinkled all over. Matt bought us gym memberships last year and I'm the only one that stuck with it. 

 

Now people do double takes on the street. I grew out my hair and my makeup looks great. I've got a runner's body,thin but a great ass from the jogging and squats. 

 

It was New Year's Eve and I decided to go for a really early run deep in the mountains. Driving took an hour alone,good thing I woke up at 4am. I love nature, and the quiet of the Dawn. I parked the furthest my car could go in, no signs of anyone else. Stretched, and I was off. There's no feeling quite like running through the woods alone at dawn. I ran for about 5 miles off the path and found a beautiful spring. 

I felt bold so I stripped and went for a dip. The cold felt great. My hot sore muscles instantly soothed by the pure water. I began to play with my uncut cock. One hand jerk in myself, the other playing with my sensitive breasts. I felt like one with nature. I was so close to cumming when I heard a twig snapping nearby. I quickly turned to see a large man on the other side of the spring. I quickly jumped out and grabbed my clothes to conceal my cock and breasts. 

“Do you mind!” I shouted and waited for the man to turn away… but he didn't. 

“You’re on private property.“ said the 6’ tanned hunk. He was very handsome and had the sexiest stubble. He was wearing loose running shorts and I could see a sizeable erection in his pants. His arms were like pythons, thick and strong. His calves and thighs were huge and hairy. But his chest was the thing that stood out the most. It was huge. Broad. And again, tan and hairy.  

I turned around and quickly put on my sports bra, panties and shorts. The man was walking closer. 

“I liked what I saw.” He said with a devilish grin. 

I blushed, quickly put on my running shoes and began to run away in embarrassment. 

My five mile run back felt quicker, maybe because I was running faster to get away from that awkward situation. 

When I got to my car there was a note on the windshield. 

_ You're fast, but I'm faster. Text me 781-555-6789 _

_ -Derek _

 

I looked around to see if there was any sign of the man. But there was not. I put the note in pocket and drove back to my disappointing boyfriend. 

 

When I pulled into the driveway I felt super horny and was hoping that Matt would be up for some frisky fun. I was sadly disappointed. He had just gotten a call from his boss telling him that they were denying his request for a raise and were even cutting his hours. He was in tears. 

I was not in the mood for this. I quickly showered and left to Starbucks to do a little work. 

I had just picked up my coffee when I remembered the note. I took it out and typed the number into my phone. I called, hesitated, and quickly hung up. 

Was I really going to go through with this? Was I going to cheat on my boyfriend of 4 years? I didn't even know if this man knows of my secret. I was naked in that spring, but my cock was underwater. Would he like me if he knew? 

 

Within a few seconds my phone received a text. 

_ Hey is this the beauty that was swimming in my spring?  _

He still thinks I'm beautiful. I better proceed with caution. 

_ It is. Sorry I tress passed. I didn't see any sign on any road.  _

 

_ No need to apologize beautiful, the view you gave me more than makes up for it.  _

I blushed again. 

_ I'm Stella.  _

 

_ Derek.  _

 

_ So you like running in the mountains eh?  _

_ Do you live close by?  _

 

_ Actually I live by Beacon Hills University.  _

 

_ Wow really. Do you attend there?  _

 

_ No I went to ucla. But currently living in the area.  _

_ Was your house nearby the spring?  _

 

_ Pretty close by yeah. My bachelor pad is just a feels miles from there.  _

 

_ Ah so you're single?  _

 

_ I am. Are you?  _

 

I stopped texting. My feelings of guilt returned. I didn't know what to say.

 

_ I don't care if you're single or not. I'll say it again. I liked what I saw.  And baby.  I saw everything.  _

 

I blushed again and my heart started racing. 

 

_ You did?  _

 

_ Yes. I did. And let me tell you. I never got an erection faster. Running rock hard was an interesting feeling. But u know it as well.  _

 

_ I can't believe this.  _

 

_ Believe it. What do you say. Would you like to go on a date?  _

 

And that's what made it too real. 

  
_ Derek. I don't think I can. I have. A boyfriend. _


	2. Taking a chance, playing a game

**Summary for the Chapter:**

> Stella can't seem to get Derek out of her head. She agrees to meet him for one drink!

**Notes for the Chapter:**

> I hope there aren't too many mistakes!  
> Enjoy!

It felt like forever to Stella since she sent that text.

 

_ Derek. I don't think I can. I have. A boyfriend.  _

 

She kept thinking about her quick encounter in the woods. How deep and commanding his voice was, not to mention his rock hard body. Stella was shaken out of her deep trance when her order was called. She got her drink and walked over to a table. 

 

_ One drink. Tonight.  _

 

Stella looked back at her phone.

 

_ I’ll let you know. I have to get some work done. _

Stella pulled out her laptop and googled “Derek Beacon Hills”. She scoffed and thought how silly that was. There must be a hundred Dereks in Beacon Hills County. It had been almost a decade since she left Beacon Hills to attend UCLA, and it was only a couple of months since Matt insisted they return here, promising a great potential job. That job ended up being for the geek squad. 

Google finished the search and 5 Dereks pop-ed up. Stella’s jaw dropped when she realized who she was dealing with. 

_ Derek Hale!?  _ she silently screamed to herself. 

 

The man she saw in the woods was double the size Derek was in High School. Stella remembered Derek as dreamy and lean, not hunky and beefy! The years had indeed been very kind to Derek. Their interactions back in High School were limited. Stiles was a freshman when Derek was a senior, and fate had crossed their paths once. 

The school had a mentoring program and at the end of the first day of school mentors met their mentees for the first time. Stiles got Derek… for about 5 minutes. Derek left the event early to get on a bus and go to a lacrosse game that afternoon. Still, that whole year Derek would wave at him in the halls, this happened probably a total of 10 times. 

 

Stella kept looking at his profile picture. she felt a tingle surge throughout her body and before she knew it she was texting him back. 

_ One drink. Where? when? _

 

Stella got home and was surprised to find Matt out of bed. He was in the kitchen scarfing down leftover pizza. 

“I’m going out tonight. Girlfriends.” Stella said as she leaned against the doorframe. 

“Want me to go with you sweetie?” Matt asked, face full of pizza. Gross.

“No. none of the girls are taking their…men. Girls night.” 

“Ah ok…” Matt replied. 

 

Later that night Stella was looking through her wardrobe. She picked out a nice little black dress and put on black pumps. She decided on her pair of lacy red panties and matching red bra. This wasn't a funeral after all! She got in her car and sped to the bar Derek had instructed. 

 

When she arrived at the location she found the bar was more of a 5-star restaurant. 

_ Yikes  _ Stella thought to herself. She was worried that she was dressed to… slutty for the restaurant. Her worries quickly subsided once inside. She noticed that many of the well dressed men, most of them older, were all accompanied by younger, flashy women. This place was a nice balance of classy and slutty. Perfect. 

She checked her phone and saw a text from Derek. 

_ You look stunning. Come to the end of the bar.  _

Stella promptly obeyed. 

All the men in the bar were well dressed, but they all paled in comparison to Derek Hale. When Stella approached the bar the man stood up and she was able to take in the amazing view. Derek had on perfect fitting suit. The bar area was dimly lit, but Stella was still able to see the intensity in his eyes, and how his suit bulged around his big muscles. 

 

“Have a seat, Princess.” Derek said as he pulled out the bar stool for Stella. 

 

Stella sat down and Derek pushed her seat in. 

 

“I’m really glad you decided to come.” Derek smiled at her.

 

“I’m glad I came too.” Stella replied, her cheeks blushing red, matching her lipstick. The bartender came over with two drinks. 

 

“I ordered you the finest rosé they had.” Derek said, handing Stella the drink. “Thought this sweet drink would match your delicious self.” 

Stella couldn’t believe Derek had just said that in a room full of people. She looked around but everyone was too busy in their own conversations to have heard. 

“What do you do Stella?” Derek asked as he enjoyed his own dark drink. 

“I um…” Stella hesitated. “I do freelance design stuff, digital. But it’s more of a side project.” Stella stopped talking and found herself embarrassed. Matt wasn’t getting anywhere in life and she would be fooling herself if she allowed herself to think differently of herself. “But I to tech stuff from home mostly.”

“You mean like coding?” Asked Derek. 

“No…” Stella answered while she blushed harder than before. She was going to die of embarrassment. Good things the bar area was not as well lit. “tech support.” 

“That so?” Derek smiled as he finished his drink. “Well maybe you can come over and help me out sometime.” 

“I have not helped someone out in person in a long time.” Stella admitted. But she was excited that Derek seemed interested. 

“What do you say we go for a drive?” Derek asked, and noticed the hesitation in Stella’s body language. “Just a quick one?”

Stella smiled and finally agreed. 

Derek dropped two hundred dollar bills on the counter and we left. 

Outside of the restaurant there were many men with their younger ladies waiting for the valet. 

A brand new black Chevy Camaro pulled up. A skinny teen got out of the car and handed the keys to Derek. 

“Here you go Mr Hale.” said the teen as he hurried off to get some more cars. 

Derek opened Stella’s door and she got in the car. She sank into the comfortable leather seats, her dress was short enough that part of of her legs touched the cold seat. That coldness along with the thrill of being in Derek’s car was sending shivers all over Stella’s body. 

 

Derek pulled out of the restaurant parking lot and sped up the street. Stella could hear and  _ feel _ the engine roar. The vibration did something to her, her sensitive balls rubbed together giving her the start of a hard on.

 

“What do you say we play a game?” Derek asked, glancing over at the beauty in his car.

“What kind of game?” Stella replied, trying to keep the cool in her voice. 

 

“I’m a gentleman and I won't make you do anything you’re not comfortable with on our first date.” He could tell Stella was still tense. “That being said I know you’re interested in more or you wouldn't have jumped in my car.”

 

Derek waited for a response but Stella stayed quiet. The night was dark despite it being a full moon. 

Derek extended his hand and Stella gave him hers. They held hands. Stella was not expecting them to be so big and rough. They felt good, like a man who has worked all his life. 

“How big is your boyfriend's cock?” Derek asked bluntly.

“Um…” Stella hesitated. “We’ve never measured his. But I know mine is 6 inches and his is smaller.”

Derek let out a roar of laughter. “Are you kidding? That’s not a man baby.” He continued laughing. “This is a man.” He guided Stella’s hand to the front of his pants where he had a raging hard on. 

Stella let out a yelp. Her hand could barely go around the man meat tucked in Derek’s pants. 

“How… how big is it?” She asked, still squeezing it, trying to get a feel of just how big it was.

“So that’s the game. If you can guess just how big it is I’ll reward you by sucking your cock.” 

“Sounds good.” Stella replied, continuing to feel Derek up. 

“Now you’ve thrown a wrench in the game since you’ve already told me how big your cock is. So how about you blow me if I can guess the color of your panties?” 

“Sounds fair…” 

 

Derek pulled over in the middle of the woods. Perfectly private. He turned on the interior car lights. 

 

He spread his legs a bit and guided Stella’s hand down further. “I haven’t cum in 4 days and these boys are full.”

“They  _ feel _ full.” cooed Stella. 

 

“Ok, Ladies first…” Derek said, still enjoying how Stella was groping him. 

“Hm…” Stella groped Derek harder for effect. “I’m going to guess… 9 inches.”

Derek looked at her with a devilish grin. He turned off the lights.

“Why did you do that?” Asked Stella. 

“So I can’t see what color your panties are.” He said as he reached between Stella’s legs and pulled off her panties in the dark. “Let’s get in the back.” 

They got out of the car.

“Lay down in the back.” Derek commanded. Stella obeyed, her dress was lifted up and her firm cheeks touched the leather. Derek got on his knees outside by the door. The moonlight allowed him to see Stella’s pretty little cock well. 

_ No way she was 6 inches _ he thought to himself. But he liked how much precum had built up already. He also  _ Loved _ that Stella was completely hairless down there. He took Stella’s cockhead into his mouth and savored the taste. 

Stella immediately began moaning and grinding her hips. She loved the sensation of Derek's beard on her sensitive skin. Derek sucked slowly, felt so warm . She’d never gotten a blow job this good. Derek stopped sucking her cock and moved down to her smooth little balls. Kissing them gently and sucking on them. Stella convulsed and screamed at she came hard. Derek had found her sensitive spot. He quickly moved his mouth back to her spurting cock and sucked out all the cum he could. He could swear that her cum tasted like fresh berries. Stella was out of breath. He pulled her close and kissed her, they both savored her cum together. 

“Oh god, I forgot how good those could be!” Stella exclaimed when she regained her composure. Derek got up and popped the trunk to get something out. “What are you doing?” 

 

She walked over and noticed a ton of power tools in his trunk. Derek found a tape measure and handed it to Stella. He turned the light on and pulled down his pants along with his briefs. Stella quickly lost her breath again taking in the sight. Derek’s hairy thighs were  _ Massive! _ Huge. But what surprised her the most was his enormous monster veiny cock that curved upwards. Stella was frozen, ogling this throbbing, uncut monster. 

 

“Measure it.” Derek said with a satisfied grin. Stella placed the end of the tape at the base of Derek’s cock, she rolled it all the way to the tip. “12… no… 12 and a half!?” She said in disbelief!

Derek had a goofy sexy smile on.

“But… that means I guessed wrong.”

“You did baby. But what kind of a man would I be if I denied any pleasure to a perfect lady like yourself?”

“Stop… you’ll make me blush again!” Stella said, relaxed and smiling. 

 

“It’s your turn…” said Stella.

“Red.” Derek answered. “There’s no way a sexy, passionate woman chose any other color for this night.”

“Correct.” Said Stella as she reached forward to grab the throbbing cock. Her hand couldn't go all the way around the thick cock, she was concerned. “I’ve never sucked anything this big.” 

“It’s ok baby. Just try… you have me so worked up it won't take much.”

Stella started by kissing the big throbbing cockhead, she let her tongue pull back the foreskin as she slowly and delicately savored the cockhead. She started sucking on it and Derek tilted his head up and started moaning softly. She kept this up for a while, also using both her hands to stroke the massive manhood. She tried taking it down her throat but failed, he throat was not used to something this big, she started choking on it.

“It’s ok baby, you did so well. I don't want you to hurt your jaw.” Derek said, lifting up Stella’s face and seeing her red lipstick all messed up with drool just like his cock. “Can I hump you?”

“Hump?”

“Yeah, I never fuck on a first date.” Said Derek with a straight face. 

“Yeah ok! said Stella as she got back in the car and laid down. 

“Keep the dress on.” said Derek as stripped his clothes and shoes. He was completely naked. He climbed on top of Stella and began kissing her neck, his fat cock pressing up against her tummy. He ran his hands along Stella’s sides, groping her hips. Stella moaned, she loved feeling the intense heat coming off of this hairy stud!

Derek’s humps were slow but strong, Stella reached down to guide his cock between her sensitive balls. Her moans got louder and that turned Derek on so much. 

Stella could hear the car squeak as Derek pounded down. 

“I… I think i'm gonna cum again.!”

“I’m going to cum too baby!” roared Derek. 

They both held each other right and moaned as they both shot. Stella spurt out three shots, but they only went up to her belly. Derek lifted up, his first cumshot hit the window behind Stella , the next one hit Derek’s chin. He shot again, this time getting Stella right in the face, she closed her eyes and enjoyed her facial. She felt two more shots hit her face, then she started feeling her dress get soaked in the stuff. The strength of his cumshots subsided, and his cock leaked a big puddle onto Stella’s tummy. 

Derek grabbed his shirt and handed it to Stella.

“Sorry about that…” He said as she wiped off her face. “4 days worth remember…”

“That was insane!” Stella explained. “I’ve never seen someone shoot so much!”

Derek turned on the light, Stella looked at her little black dress, which looked more like a little white dress now.

“I’m sorry i ruined your beautiful dress.” 

“It’s ok…” said Stella. She looked over at the clock. It was only 11, Matt would still be up. “but i can't go home like this.” 

“Want to cuddle? Kill some time?” 

“Yes.” Stella replied, and kissed Derek as she stripped off her dress. 

Derek did his best to wipe up the seats. He traded places with Stella and lied down first, and let Stella get on top of him. She placed her head on Derek’s strong hairy chest and once she got used to the ticklish hair she focused on his strong breathing. And in no time she was asleep. 

Derek remained awake for a bit longer. He lightly scratched Stella’s back and kissed her head. The car smelled so strongly of sex. Derek was genuinely happy. He had the woman of his dreams in his arms, now he just had to win her over. 

 

**Notes for the Chapter:**

> What did you guys think? :)

**Author's Note:**

> I hope it wasn't too bad!


End file.
